The Not Very Subtle Plans of Dean Winchester
by Ockermuller
Summary: Romance, AU. Convinced his brother is pining after Gabriel, Dean decides to unleash his genius matchmaking plans on the world. Cas just nods along. Sam/Gabriel, Dean/Castiel


**Title: **The Not Very Subtle Plans of Dean Winchester.

**Beta: **The awesome Kodamasama (kodamasama . livejournal . com )

**Recipient: **Mistalagan. For the Secret Lovers Exchange!

**Rating: **PG-13.

**Genre and/or Pairing: **Romance, AU**. **Sam/Gabriel, Dean/Castiel.

**Spoilers: **Up until stuff revealed in 5x08.

**Warnings: **None I can think of.

**Notes/Prompts: '**Matchmaking fic, with Dean as the instigator.'

**Summary: **Convinced his brother is pining after Gabriel, Dean decides to unleash his genius matchmaking plans on the world. Cas just nods along.

*º*º*

"Look at them." Dean shakes his head disapprovingly. "Clueless."

Cas squeezes his eyes and tilts his head as if searching for whatever his friend is talking about. "I don't follow; they're just talking."

"_No, dude_. They're pining after each other." Dean rolls his eyes. "It's fucking obvious."

A few tables away, Sam and Gabriel are too busy biting each other's head off to even notice their brothers are there. Dean always says someday they'll make arguing into a national sport - although, despite the ever present edge on their interactions, nowadays they even look like they're having fun.

But that's it, Castiel thinks. Just two people who enjoy debating and appreciate a strong opponent.

"You must have magical observational skills then, for I see nothing," Cas concludes.

"Look, look at the hand gestures. I haven't seen Sam so excited since he was in high school on the debate team. They're even leaning towards each other."

Fact is, their bodies _are _constantly leaning into each other's personal space, and they probably don't even realize it. Gabriel is the sort of guy who makes a show out of telling a story, complete with unnecessary touching and exaggerated hands gestures, so it figures he's always touching Sam's arms and knees as he talks… but he does it on impulse, so for Castiel it means nothing.

Sam too seems more tolerant - less annoyed, that is - by all the attention than he did a few months ago. Maybe they're finally developing a friendship out of their time together discussing movies over coffee, but that hardly means they have secret feelings for each other.

"They're just arguing," Cas says. "It makes them exited."

"That's like foreplay to them."

"Sam looks angry." And he does. The attractive lines of his face are rigid as he listens to whatever ridiculous things Gabriel has got to say this time.

"It's all the sexual tension between them. It finally drove him mad."

"Or maybe they're just two closeted 'Dr. Who' fans who finally found each other and now can't stop arguing over who's the best Doctor," Cas muses after hearing the words 'David Tennant' three times over coming from their brothers' direction.

Dean rubs a hand over his forehead. "God, I'm surrounded by geeks. I've got no idea what you just said. And your conspiracy theories are really boring, did you know that?"

"At least mine aren't based on unlikely romantic matches." Cas drinks his coffee.

*º*º*

"You coming over for pizza tomorrow?" Dean asks, throwing himself on Sam's couch like his brother's house is still his own.

"Hm, no." Sam looks through his bills distractedly. "I'm going to a _vernissage_."

"…A what of what?" He snorts. "Since when are you refusing pizza on a Saturday?"

"_Vernissage_ is the opening day of an exhibition. I promised Gabe I'd go with him." Sam smiles apologetic. "Sorry, we'll get pizza next week."

Dean raises an eyebrow.

"'Gabe'?"

"What?" Sam looks at him confused.

"He's 'Gabe' now?"

"We're sort of friends." Sam pauses, considering. "Frenemies."

"Dude, c'mon!" Dean laughs. "You realize you guys got a thing going on, right?"

Any discomfort he feels for talking about his baby brother's gay relationship with a loud-mouthed little idiot is worth it just for watching Sam's ears turn red in embarrassment.

"What do you mean?" Sam stares at his shoes, probably praying for a phone call - or at least a small earthquake - to interrupt their conversation.

"Sam." Dean sobers up for a second. "You know I don't care if you have a crush on the guy. I mean, I'll tease you forever, but you know I don't mean any of it."

Sam can't help but smile at that. Dean is surprisingly awesome sometimes.

The oldest Winchester grins. "Besides, your level of gayness was confirmed years ago."

Unfortunately, he also doesn't know when to shut up.

"It's that obvious, hm?"

"Like a comb over."

It's been a few weeks since Sam made peace with the fact that he thinks Gabriel is cute. Because he is, with his casual touching, pouty mouth, cheekbones that rise when he smiles, and a smirk that promises things Sam never knew he wanted.

And Gabe is pocket size, for God's sake. How can Sam not like a guy who's always looking up at him with a smirk on his full lips like he's enjoying the view from down there?

Sam has always been a sucker for cute people who need to put a hand on his chest for balance so they can get on their tiptoes to kiss him. Not that Gabriel has ever indicated he's interested in kissing him – actually, hazel eyes _were_ constantly staring at his lips, but maybe the reason behind it is just Sam's wishful thinking - and yet imagination exists for a reason, and he likes to think Gabe would be the type who enjoys leaning on a firm chest as someone sweeps him off his feet and carries him to the bedroom.

_That _is another peculiar thing about his feelings - Sam has never had so many fantasies before meeting Gabriel, all of them beginning the moment he allowed himself to like the shorter man – as if an entire world of sexual kinks he never knew existed was suddenly born inside his head.

At first, he imagined a Gabe with no inhibitions - who uses Sam's body for his own pleasure, taking it all for himself and lying on his chest after he's done, completely satisfied. In other fantasies, he's the sort of guy who still has control even if pinned to the bed by a body twice his weight. And because he knows that, he allows himself to be manhandled and looked after, letting his partner take care of everything for him… And would Sam take care of him-

And okey-dokey… Sam's got it bad; he's not denying anything at this point.

"I- I think it's a little more than just a 'crush'," he confesses. "I haven't felt this way since Jess."

If there's anyone who knows how big this is, that person is definitely Dean. Sam hasn't committed himself to anyone since his first girlfriend, Jess, died in a fire when they were in college. It took him two years of mourning and his brother convincing him to move back to Kansas for Sam to consider dating again. However, his lack of enthusiasm for his partners meant relationships never lasted long, and he couldn't help but feel disappointed in himself for letting them go so easily.

Sarah had been nice – too nice, like she believed she could fix Sam with rainbows and perfect dates when he hadn't been broken to begin with. Madison had turned out to be a different person than he thought, Ruby had _definitely_ turned out to be a different person than he thought, and Dr. Roberts hadn't even been worth a second date.

"_Dude_…" Dean mutters surprised.

"I know," Sam agrees, sighing. "Just… don't tell him anything…"

"What do you mean 'don't tell him'?" He sits up straighter on the couch - his usual stance when he's getting ready for an argument. "You are going to _do something_ about it, right?"

"Not really-" The taller man shrugs.

"Sammy, you have _feelings_ for this guy! I haven't seen you so happy since you found out banana chocolate chip is an actual ice cream flavor!"

"He doesn't feel the same." Sam shakes his head. "I don't want things to be awk-"

"Are you joking?" Dean is raising his voice as he gets up to make himself look bigger, a gesture reminiscent of the time he was taller than his younger brother. "Are we talking about the same person here? The guy is totally gay for you."

"You don't know Gabriel, Dean. If he was interested, he would have let me know by now."

"Dude, listen to me-"

"No. He's the first friend I've made since I got here; I'm not going to make things awkward between us," Sam decides. "I don't want you meddling."

"You're being stupid-" Dean starts, but stops when he realizes Sam is actually serious about this.

Sam fixes his brother with a hard glare. "We already had this discussion. If I don't want to date someone, it's none of your business."

Like fucking Hell his baby brother being a dumbass isn't any of Dean's business.

*º*º*

"This is bullshit. I gotta do something."

Dean gets inside the apartment before Castiel can even make room for him to walk in.

"Until you decide to make sense, I'm jut going to pretend you're not here," Cas informs him. He doubts his friend is even listening.

*º*º*

"Traffic is insane; I don't think we can make it in time. Sorry, man. Are you already there?"

"Yes, Dean." Sam slumps in his seat. "You could have told me sooner; Gabe is going to be here any minute now."

"I'm sorry, jeez… You know what, you guys go ahead and watch it. It's one of those artsy bullshit movies I hate anyway; I only agreed to it because Cas is such an art geek."

"Photographer-" Castiel's muffled voice comes from the background.

"Yeah, yeah," Dean interrupts his friend from protesting, "So, you guys have fun!"

Dean sounds way too happy for someone stuck in traffic. Although his brother's not even in the same room as him, it doesn't stop Sam from putting on a suspicious expression - AKA 'I-know-you-are-up-to-something-Dean' Bitch Face. He directs it to the table just to avoid misunderstandings with the other patrons.

"Won't Cas be upset?" he asks.

"Of course not. Wait- Cas, tell him you don't care."

"I still think this is pointless-" There are a few sounds of the cell phone being moved around until Castiel's voice becomes clearer. "Hello, Sam. I'm sorry we won't be able to make it. You and Gabriel should go ahead and watch the movie without us," he says as if reading from a script.

Whatever Sam was about to say next is lost when brown hair and a dark red coat appear in the corner of his eyes, catching Sam's attention completely. In just a moment this pleasant, nervous feeling turns in his stomach - the same one he had as he waited in line to ride a roller coaster for the first time.

Gabriel finds him immediately – not so hard to miss the giant sitting by the window – and makes his way over with a small smile on his lips. Sam prays he doesn't look too stupid sitting there smiling back like a retard.

"Okay, I'll talk to him." Sam hangs up with a sigh. "That was Dean. Our brothers are blowing us off."

"Why?" Gabriel sits down and doesn't waste any time before reaching for Sam's coffee on the table.

"He said they were stuck in traffic, but there were no traffic noises, so my best guess is that they finally got a clue and will now proceed to make out in the Impala."

Gabriel takes a moment to contemplate this. "They're not very good at subtlety, are they?"

Sam stares. "You have a sticker on your car that says, "If you've got a problem, talk to your congressman". You don't get to say what's subtle."

"Touché, Big Bird." Gabriel sends him his kilowatt smirk, the one that makes his features look younger and… _attractive_, and Sam wonders when he stopped caring about the stupid nicknames and started to focus more on the glimpse of white teeth he got every now and again.

Silence follows for a few moments as Dean's voice isn't there to guide the conversation. It's just the two of them now, and Sam still has to ask Gabriel what he wants to do. The image of them sitting side by side in a dark, empty movie theater appears in his head, and his heart tightens at how much he suddenly longs for the intimate company of a date.

"Still want to go?" Sam asks and discreetly wipes his sweaty hands on his suit while he puts his cell phone in a pocket. He quickly adds, "I heard it's a good movie."

"Sure. We came all this way…" Gabriel shrugs. "But since Cassie isn't here, I wanna sit in the back. He always makes me sit in the middle."

Gabriel makes the face of someone who just sucked on a lemon, like sitting in the middle row is too normal for him and will give him allergies.

"I like to sit in the last row too. People get bothered by my height, otherwise."

"Ow, Sam, the Friendly Giant." Gabriel says, and there it is again. Smirks that do stupid things to his body.

"Come on then…" Sam gets up and adds before he over thinks it, "Shorty."

It's completely unoriginal but totally worth it just to hear Gabe burst into laughter behind him.

*º*º*

"What do _we_ do now?" Cas asks, giving Dean more space to lie on the couch and rest his feet on Castiel's lap.

"The same thing we do every night, Pinky."

"Watch old reruns of Seinfeld and then complain there's nothing else on even though we're perfectly capable of renting a movie?"

"Exactly." Dean grins.

*º*º*

_helping cas out, wont make it, sorry dude._

"Why does he only let us know when we're already here?" Sam asks after reading out loud the message Dean had just sent him.

"Tsk, tell him to fuck himself very much," Gabriel says and makes a hand gesture to get the waiter's attention.

Sam dials. It goes directly to voice mail. "He turned off his cell phone."

"Third time this week. This is getting ridiculous. Can't they just act like normal people and admit they're going out?"

"But that's exactly it, I'm not sure that they are," Sam tells him. "Dean doesn't look any happier than before…"

"Whatever, I'm not going to complain anymore. At least now we don't have to watch them make cow eyes at each other."

A waiter stops by their table, and Sam smiles politely. "Our friends aren't coming, so we're ready to order."

"I'm sorry, sir, if it's only the two of you I'll have to ask you to sit at a smaller table."

Sam wants to protest, but his friend is already up. There's a reason he hates small tables, and Gabriel just happens to find it hilarious that Sam can't find a position that will make their legs not bump under the table.

"Just stop moving already. I don't care," Gabriel says and searches for their waiter again, looking perfectly happy with their cramped arrangements.

Sam spends the rest of their not-date pretending not to notice the comforting heat on his legs and how, as Gabriel moves around while he talks, the movements feel like intentional caresses.

*º*º*

_alarm clock is a bitch, just woke up, sorry_.

"Who was that?" Gabriel asks. He ignores the honey on the table for once and mysteriously produces his own nutella jar.

"Dean saying he's not coming."

"Oh, right. I totally forgot about him," he says and offers Sam his hazelnut treat.

Taking the small jar, Sam just smiles. "Me too."

*º*º*

Dean sits across from Gabriel in their usual coffee shop and gives Castiel a meaningful look that has Gabriel raising his eyebrows.

Apparently Castiel understands whatever it is Dean is trying to convey. "I'll get us coffee."

As his brother goes to stand in line, Gabriel finds himself alone with Dean Winchester staring at him with narrow eyes – analyzing him. He smiles awkwardly. "You okay there, bucko?"

"Okay-" Dean clears his throat. "Obviously you people can't get a clue, so desperate measures have to be taken. I'm going to tell you something and then we'll never talk about it again. Are we clear?"

Gabriel can only blink. "Are you drunk at 8 in the morning? Wow, that's pathetic," he says and leans in to smell him. Dean gives him an ugly look very much like his brother's, and now Gabriel is definitely amused.

"Pay attention; I'm not going to repeat this." Dean clears his throat again and draws a deep breath before starting. "Sam likes white chocolate, but he prefers chocolate chip cookies after coffee. He digs classic movies - like Hitchcock and Kurosawa… Hm, _pizza_! He loves pizza – believe me, he'd eat it everyday if it wasn't for his bullshit diet." Dean pauses to scratch his head, trying to remember his list. "He doesn't like people who kiss him without warning. He thinks they're rude or something 'cause he's a pretty woman like that."

Gabriel's lips are narrowed into a thin line as he asks, "And what am I supposed to do with this information, Dean-o?"

Dean only raises an eyebrow and smirks because _c'mon_.

Gabriel rubs a hand over his eyes, his facial lines making him look older and drained. "Sam is straight."

"Sam went to college. Don't people turn bisexual in college?"

Gabriel grits his teeth and turns around to make sure Sam isn't standing behind him like a stupid sitcom joke.

"No, seriously now. So far he's only gone out with women, but I can tell he has a _thing _for you," Dean tries to convince him. "Trust me, I'm the older brother; I know what I'm talking about." He stops to consider before deciding that, what the Hell, spilling the beans might be faster. "Actually, he told me once about his man-crush on you. But don't tell him I told you what he told me."

"He… said 'crush'?" Gabriel lowers his voice like they're sharing a secret. Add a card, 'Do you like me? Yes or no', and they're officially back to third grade.

Dean doesn't break eye contact as he nods. If Sam can't get a clue, maybe Gabriel will.

And just like that Dean gets all the credit. He grins to himself.

"If Sam wanted-… he would have asked me out by now-"

"Maybe he thinks_ you _would take the initiative if you wanted something." Amazing. And these two are supposed to be the smart ones. "Dude, you hit on anything with a pulse, but you never mean any of it. What is he supposed to think?"

Castiel sits next to his brother and proceeds to ignore them. The fact that Dean has been setting them up dawns on Gabriel and he doesn't know if he should get mad, be thankful, or just punch the smug Winchester for acting all high and mighty when he hasn't made his own move on Castiel yet.

Looking over his shoulders one more time, he coughs nervously. "… Go on."

And Dean does.

*º*º*

It's amazing how Sam learned to love two completely different people who turned out to be so alike. While Jess would softly rub his shoulders and ask what was wrong, Gabe throws himself next to him on the couch and pinches his side gently, saying, "Who kicked your puppy, Sammykins?"

Same actions, different choice of words.

"Tough day at the office," he offers as explanation. They never talk much about work. His job as a lawyer must look really boring for someone as lively as Gabe.

"Hm…" the shorter man agrees with a nod.

He watches as Gabriel's meticulous fingers tug on a loose thread on Sam's jacket. It's almost entrancing how they twist the fiber into a curl only to smooth it out a moment later.

"Wanna talk about it?" Gabriel quietly asks, and Sam suddenly realizes they haven't spoken in a few minutes.

"What?" His eyes reluctantly rise to look at him. "You never asked me about my work before-"

"I'm starting now." Apparently, his fingers are now bored with the thread and decide to close around his wrist instead. Only Gabe can make what's basically hand-holding look casual.

"No, it's fine. I'm just tired. It's just-" Sam trails off as warm fingers begin tracing his hand.

Oh.

_Oh._

Fuck, it feels _good_.

One of his most intimate secrets – or as Dean likes to say, his 'weird-ass hand kink' – is the fact Sam loves soft caresses on the palm of his hand, right on top of the lines. He can't help himself, and he's too embarrassed by it to tell anyone, but _damn_, it is _there_.

Except for the time he got drunk and told Dean – the bastard, always using this against him - the only person who found out about this was Jess… And now Gabriel, who has a firm grip on his right hand and is not letting go.

"Hey, Sam…" Gabriel leans against him, fingers smoothly stroking his palm. The part of Sam's brain that hasn't shut down tells him this _has got_ to be deliberate, but he can't for the life of him figure out how Gabriel would know about this. "Did you know I have a Hitchcock collection?"

"Really?" And okay, his voice sounds dumb even to his own ears.

"Yep." Gabriel grins. "Not a really big one, but it's there. Wanna come over to watch?"

*º*º*

"Argh, look at them!" Gabriel cringes just from looking at their brothers.

"They make me sad," Sam concludes as he watches Dean practically wave a journal in front of Castiel's face, probably trying to convince him to go to one of his action-filled movies with him.

Maybe they could pass for friends making plans for later that evening, but Sam knows they'll go to the last screening of the night and spend the entirety of the movie whispering commentaries to each other and pretending their hands aren't touching inside the popcorn bucket.

"Pathetic." Gabriel raises his chin and waits. Sam doesn't need any more instructions before kissing the corner of that smiling mouth.

He grins. "Clueless."

*º*º*

I wanted to include smooch but I ran out of time because college is a bitch!

Maybe I'll write a sequel to this eventually? I'll title it "The Not Very Subtle Seduction of Sam Winchester". XD


End file.
